All posts tagged life

Are Startups Cool?

I was catching up some friends and someone at the table said, “I don’t really get what you do…but it just sounds cool. Anything with ‘startup‘ in it sounds cool…so good job!”

That’s pretty much how the world thinks about startups right now.

I think that’s an unhealthy way to think about startups.

I didn’t get into startups because they’re cool, but I have a sense that people are starting to do just that.

A sad economy and bleary job prospects have made even my most risk-averse friends consider leaving their jobs to join a startup. The excitement surrounding early stage tech is so high right now that for some people “sitting on the sidelines” has become the risky career move.

That’s insane. The idea that starting or joining a startup is a rational career move is straight up crazy.

Any startup founder would agree that the last reason they got into this game was because they were thinking about their career.

My Story

An early draft of this post didn’t include much about my own experience and the few I asked to read it suggested I include a bit about my own experience. I think they’re right in that it’s helpful context. I’m not writing from the top of the hill, having sold my company for millions. My first startup is still alive but it’s a company we’re still pushing to find real success in.

I went broke as a startup founder. Dead broke. The kind of broke that people get uncomfortable talking about.

It was the kind of broke that left me unable to pay rent in Vancouver, having relocated there following our seed round. Unable to pay rent, I ended up taken in by an entrepreneur friend to crash on his couch. At 30 years old I was living on someone else’s couch without a dime in my pocket, working on our startup at every spare moment.

Every day, waking up presented two major challenges:

  1. Find a way to push our startup towards success and find a revenue model that worked.
  2. Find a way to survive by acquiring food.

If that sounds basic, it was. When was the last time you worried about eating enough?

I reached a point at which I’d ration out my week on less than 20 dollars. I was forced to ask for help from other entrepreneurs who would buy me meals. I couldn’t always feed myself.

Unable to pay bills, I stopped doing so. My credit card debt began to build all around me. My phone went dead.

The fallout of going really broke is immersive. You lose your sense of the normalcy most people experience. You’re doing it for the dream you’ve committed to, so you’re left with nothing except for the work you’re doing.

You work.

You have nothing else you can afford to do.

It’s brutal. It’s not glory.

A startup means uncertainty. Startups mean risk and pain and embarrassment. Startups can mean homelessness.

So…are startups “cool”?

Let’s look at the good and the bad. This is by no means an exhaustive look at startup life. If you’re in it, please share your insights in the comments for my mostly non-startup audience.

The Good Stuff

  • DREAMS – Creation IS cool: Building something new is cool. It’s as cool as writing a hit song or making a beautiful movie. Mainstream culture is now idealizing Sean Parker in the ways that they used to idealize The Rolling Stones.
  • INNOVATION – Risk aversion drives innovation: Startupheads are risk averse and face uncertainty in a way that most people don’t have the stomach for. Facing failure forces people to keep on pushing their boundaries. The survivors persist because it’s what they’re meant to do. That selection process benefits all of us.
  • BENEFITS – Work your own hours, unlimited vacation, blah: Startups build their own culture from the ground up, and we are lucky to have that fortune. It’s not 9 to 5. It’s a life very driven by results.
  • COMMUNITY – Altruism makes it all possible: Startup people are passionate. That passion birthed an industry full of collaboration and support that puts other industries to shame. Newbies in the startup world are met with encouragement and mentorship. It’s a competitive world, but it’s generally more friendly than other industries (I’ve worked in high finance and law, others can comment otherwise).

The Real Stuff

Here’s a bit about the stuff that isn’t “cool”.

  • DREAMS – Uncertainty is horrible: Imagine never knowing if you’ll have a job tomorrow. Or if you can pay your bills next week. Founders have it the hardest, but no matter where you are in the ecosystem, you’re always living a life that’s got no guarantees. Startups aren’t a career, they’re a lifestyle.
  • INNOVATION – Failure, always: In a startup you’re always fucking everything up. There’s nowhere to hide; you will feel bad at your job. You will often go to sleep knowing you could have done more. You will always know how much more there is to do. Everything but work can become “not working”, if you aren’t working.
  • BENEFITS – Paychecks are unstable: In Startupland, salaries are kind of a joke. Being an early team member on an unproven technology venture means you may find yourself elated every time you get paid. Financial instability is pretty consistent and it affects nearly aspect of a startup team members’ life.
  • COMMUNITY – You don’t complain: Whether you’re a founder or an early employee, every early stage ship is a rocket ship, and saying otherwise is sacrilege. There isn’t a lot of room in the startup culture to complain about your job. Startup jobs aren’t jobs. They’re tribe memberships.

I think it’s important to recognize that joining a startup is an admirable endeavor, but it’s equally important to acknowledge that it’s not for everyone. In fact, it’s not for most.

Startup work is a mishmash of incredible strength and passion living right next to complete uncertainty about a final outcome.

That uncertainty is the result of a 99% chance of dying early. Have you ever taken a job with a company you expected to fail?

That’s a prerequisite to working in Startupland.

I’d love to hear more thoughts on the hype I’m seeing around being a part of Startupland. We need to talk about how hard this is. We need to recognize that we’re all choosing to struggle.

If we deserve the accolades that we get when we succeed, we should honor and celebrate the challenges we take on for what they are.


Where I’ve Been & Where I Am

A big thanks to everyone who still finds me invading their inbox or RSS reader.

I’m going to be writing a lot more going forward, but things will change a bit. It’s like that time you told your dog she was going to the park and really you were taking her to the vet.

(Your intentions were great, by the way.)

I’ve always written extensively about my relationships on this blog in the past, and I’m not sure that will go away. I can’t really write without including the deeply personal stuff.

But…I am sure that I’m a different person than I was when this blog started. I’ve gotten into the frame of mind that nearly anything is possible if you dive in head first, learn as much as you can as fast as you can, and stay close to amazing people.

The last few years have been transformative, and I’m passionate about the role that technology plays in our lives. I need to explore that with you, and I hope that while I do that it will benefit you (no matter how much you think about tech).

As to the title of this post, I’ve been through the amazing process of being a first time startup founder. To all the people out there who’ve started businesses or hope to start one some day, I’m going to do my best to share my experience (finally).

Today, I’m working on another startup that two friends founded, hell bent on helping them turn their already measurable success into a true game changer. It’s brought me back to San Francisco, a city I adore on every level and a community I’m deeply excited to be a part of.

Going forward; moar writing.

If you aren’t getting rejected on a daily basis….

One of the great things about looking for a job is that your “payoff” is almost always a max function (the best of all attempts), not an average. This is also generally true for raising VC financing, doing bizdev partnerships, hiring programmers, finding good advisors/mentors, even blogging and marketing.  I probably got rejected by someone once a day last week alone. In one case a friend who tried to help called me to console me. He seemed surprised when I told him: “no worries – this is a daily occurrence – we’ll just keep trying.”  If you aren’t getting rejected on a daily basis, your goals aren’t ambitious enough.

via If you aren’t getting rejected on a daily basis, your goals aren’t ambitious enough – chris dixon’s blog.

This is how to be successful. Bloggers should take note, as should entrepreneurs.

This Monday As A Monday

Sleep at two am because I still can’t breath 100% and sleeping when you’re breathing out of a straw isn’t even really sleeping and it definitely doesn’t come easy.

Wake up at seven in a deep sweat and almost no idea what day it might be or what time it is or what that goddamn blaring, oh…my alarm. Time for today.  Feeling robbed of some post-sickness sleeping.

Strategy meeting first thing, maybe push it back…got a pitch prep session at nine thirty…every day this week.

No time for a shower, out the door hoping I’d get a minute at some point to sneak up to the fitness center I joined for the winter. I rounded corner to a bus pulling away. Oddly another rolled up a minute later and I sat in the back where this woman carefully applied her makeup as we rolled into downtown and for a moment I remember thinking I was pretty happy to not be worried about some things.

As I write it’s around eight pm and I’m headed to North Vancouver in an hour to pick up a generously donated dresser from Maura and Danny.

Home by ten or so?

Yeah no workout.

Investor pitches coming together alongside a day full of annoying delays on a video I needed done today and literally just finished. Early afternoon conference call about a nationwide social media campaign we got involved in through the end of the year. Explained the value of twitter, outlined strategies.  Missed lunch.

Every spare moment in the office is about tomorrow and our company and its people and its impact and its dream.

Took a walk around the block mid afternoon so I wouldn’t throw my laptop through a window, wouldn’t overanalyze things, wouldn’t starve…wouldn’t someday look back on this day and this time and wonder where the hell it all went.

Wishing I’d showered at the moment, honestly.

How was your day?

Tell me good things.

Work On Something Cool

You find yourself in the middle of a day that’s a month after the one you last remember.

You want to have written every minute of it, but instead you look around and wonder what you might do to further the cause you’ve jumped on board with.

That’s the best part of working on something you care about.  It’s also bad for your personal blog.

No, that isn’t an apology.

I spent a lot of time in the years after I graduated from college wondering what real people did with their lives.  I looked at the routes society mandates as advisable and found most of them completely foreign to the way I operate.

So I tried a few things.

I tried working for a lawyer doing deals in Hollywood and pondered the potential of a life as an intellectual property attorney.  Flights to LA for movie set duty and daily check ups on the industry news in Variety.

I took the LSAT twice and that second time I killed it like oil killed the Gulf of Mexico.

Before I got my scores back I heard the sing song everyone in the industry offered as advice: we hate this work.  I worked for people I saw gripping smoke and coffee breaks like their day would explode without them.  I saw the promise that going postal would provide wickedly smart people locked up in the depression afforded to the unfortunate and well-meaning people who settle for the restrictions of a typical career in a typical industry that pay a typically great salary for being typical.

Out I went, chasing the promise of an entrepreneurial environment in an identically typical industry.

Where I learned the hardest lesson I’ve learned: working for yourself isn’t the promised land.

Working for yourself isn’t the same as working on something you love working on.

So I failed at a long term and scalable business effort in a field that didn’t make me happy.

Big surprise there.

Today I’m in the office at the heart of a truly gorgeous city pretty damn late on a Friday night, and I feel like working.

I feel like working.

Hours and hours after I’d ever have imagined working on anything remotely related to work at any point in the years that came before 2010.

It ain’t easy.  I’ve told a lot of you that.

Take it from me though; life’s work and work’s life.  You are both.

Make ’em jive.

Work on something cool. Do it in the morning or night or lunchbreaks or whatever.  Just do it.

Then tell everyone about it.

What are you doing that’s cool?  I truly want to know.

A Calendar Of Question Marks

At the end of September, I moved out of my apartment on Division Avenue in Wicker Park and in with one of my best friends, Braden.

I haven’t lived in a place I’d call my own since.

Living in the domain of other people is something you get familiar with in college.  It’s a unique experience for most; those of you who went to boarding schools or those fancy East Coast prep schools were rocking the roommates even earlier.  Maybe boarding schools and prep schools are the same thing, actually…honestly I’m just a Midwest guy who played soccer and passed Calculus.

Either way the Rules of Life’s Trajectory usually dictate a point at which you don’t live in another’s domain at some point in your mid-twenties.  I did rent on my own in Wicker Park starting at about 25 or so, and I did love it…I reached the point of no return on living with roommates.

I thought so, anyway.

Ironically, living with Braden was a lot of fun.

It was kind of like a vacation in some ways, and at that point I had quite a bit of uncertainty in my life and couldn’t have made it through that without his generosity, so if you’re following him on Twitter I wouldn’t be upset if you sent him naked pictures or money.  Back then we were already spending most of our free time together and it saved us the four blocks walk between our places, which is pretty significant once it’s December and Chicago is frozen solid.

Since arriving on the Left Coast I have stayed in three different places (as of this weekend).  I’m still transient, and it’s been so long that I’m pretty darn comfortable with being transient.  It’s amazing the way life just sort of happens, and you can get comfortable with the way things were or you can let Change influence tomorrow.

My tomorrows are largely dictated by the almighty Change, as it were, and at thirty years old I feel a combination of irony and comfort with the whole thing.

I never thought I’d be thirty and living in a new city with a bunch of question marks sitting on my calendar.

I also can’t say I’d feel any more comfortable with an alternative path.

When I think about a few years ago, in a serious relationship (with a wonderful girl) and trying to put together pieces of a future in Chicago, I know that even that life was chock full of question marks.  When I read all of the wonderful bloggers I’m fortunate enough to follow; people of all ages and walks of life; I see one common thread…tomorrow’s not always what you thought it’d be.

I’m not knocking stability.  I do wish I had more, sometimes.

Yet, there’s nothing traditional about the lives of the people I know.

Even the people I know who have traditional jobs or traditional love lives or a measure of habit and repetitiveness in their days.  Even my parents, who’ve been in St. Charles for more than twenty years, still manage to face total chaos somewhat regularly.

People get pregnant, sick, fired, and bored.  They write books and get promoted and take vacations that change their lives.  They get into grad school and drop out of college and follow their instincts.

The only thing that remains constant is how mixed up and crazy the world can be.


I rolled off the highway into the neighborhood that’s the only one in Chicago that’s ever felt like a hood to me, and I was at the tail end of a trip downtown to likely spend as much time parking as I’d spend sitting at the restaurant with three or four old friends for an hour catching up.

I’d been frantically juggling scheduled and unscheduled phone calls for an hour and having gotten in the car on the phone, called my father upon hanging up, and parked while updating him on my somewhat unpredictable life-landscape, I got out of the car to pay the ridiculously overpriced box thing only to find it broken.  I looked down at my phone, arguably to make sure I hadn’t dropped it when I got out of the car (necessary for a guy like me), and found out lunch was canceled.

I rolled off the highway into my ‘hood with thai-food leftovers in my head (like sugarplum, but spicy) and saw a man in his fifties with his left arm holding the rail in front of a townhome, leg cocked and ankle resting on his knee while he bent over and adjusted his sock.

But he wasn’t adjusting his sock, he was dusting it off.

His musty blue wind-breaker and off-sized brown trousers spoke in subtle tones around his worn attire and his scuffed untied broken down black sneaker waited patiently on the pavement for the impromptu cleaning to be finished.

I took my foot off the gas pedal and let my gaze briefly lock in on his world as my car slowly rolled past, never able to see his face but witness to his strength and struggle in a world without a home.

Photo by pedrosimoes7.

Take A Second

I’ll admit to being at a point in my life in which things are a lot harder than they were a year, even two years ago.

There aren’t many places to hide from what’s happened in the United States over the last eighteen months, and I would think that’s true around the world.  I work extremely close to the epicenter of the seismic shift that happened around the Fall of Wall Street not long ago.  Every civilized nook and cranny on the planet felt the ripple effect.

Sure, it’s not part of everyone’s daily life, but we all know it’s out there.  We all know someone who’s in a challenging employment situation.  You might even know someone who’s had to change one or two of their habits or plans because of the way the world reshaped itself overnight.

I don’t mean to be depressing.  To suggest that life is miserable and we should all go cry ourselves to sleep.  However, I”d be hard pressed to agree with you if you suggested to me that the average (or median) barometer on society’s general well-being hasn’t slipped a bit as we wade through a recession that’s covered the globe in a blanket of systemic difficulties.

Now, it’s easy to get caught up in that.  It’s easy to let your lens get dusty; tough times kick up dust, and hiccups seen through dusty glasses tend to look like crises.  Difficulties seem to sharpen into focus and the good stuff seems blurry.

I’m saying this because it’s been my own experience.

Earlier this week you should have heard about Jaycee Dugard, who was kidnapped by a sex offender 18 years ago and lived in isolation, in a hut, until discovery this week.  Jaycee emerged with two daughters, 15 and 11, both fathered by her abductor.  You can read more here, if you haven’t eaten.

Outrage aside, her story has gutted my perspective.

The world is a big, big place, and sometimes I think we young adults forget how great we have it.

I know…that’s a little played out, and the ‘you’re so lucky’ chorus risks condescending overtones, but when I read Jaycee’s story I literally felt sick having lately felt as if I deserve to have things go easier on me.

As if my problems had any real relevance to the ultimate human struggle.

This women just joined the world as we know it.

She is twenty-nine years old.

Between today and my eleventh birthday, I’ve had hundreds of friends.  I’ve had a handful of loving relationships with beautiful women.  I’ve played soccer in ten different countries, and in front of hundreds of thousands of screaming fans.  I’ve learned about foreign cultures, political histories, emerging technologies, social causes, and human potential.

I’ve spoken to my mother and father over and over and over again.  I’ve watched my sisters grow up into truly incredible young women who each has the potential to make the world a significantly better place for other people.  I’ve gone from hating family trips to Upstate New York to a man who values my relationships with my 40+ cousins more than he ever thought possible.

I’ve developed a taste for single malt scotch, avocados, and sushi.  I’ve been in two car accidents that should have killed me, and emerged unscathed from both.  I’ve had coffee with the President’s daughter and I’ve debated everything under the sun with a myriad of different people with different backgrounds and diverse perspectives.

I know how to type.  Fast.

I have been disciplined for treating other people badly.

I’ve mended a broken heart.

More than once.

My struggles were faced with a web of support and resources every step of the way.  Through the total devastation in fifth grade at the friends chosen for the other middle school, through the broken foot I thought would forever derail my soccer career, and the mononucleosis that nearly did.

The day I lost my first job.  The pain of watching friends go through worse; divorce, eating disorders, abuse, suicide watch, and mysterious illnesses.  There were people to call.  Without fail.

I’m not preaching here.  Jaycee’s story stopped me in my tracks.  That was my experience and doesn’t have to be yours.

If you do take a second to look around, though…to try and imagine your life matched up next to one with an eighteen year stint in one room in an overgrown backyard…

…tell me what you see.

(A bit of a tribute: if you have any “since I was eleven” sentiments in light of Jaycee’s story, tweet them and use the hashtag #sinceiwas11JC.)

Photo by nyki_m.

What The Who

I’ve reached the point at which I just am the internet.

I’m at the tail end of eight months of planning a blogger meetup in Chicago, most of that time spent circling back and redoing nearly everything I’d already done or set in motion.  You want to talk about an “I’d do it all differently if I started over” feeling?  Multiply that by the number of Skittles in the world and you might be able to see me up here on the moon dancing around in my space suit mumbling incoherent truisms about digitally savvy millennials.

If you fall into the category of a young adult who’s online interacting with your peers, and facebook friends, and famous people on twitter, and creepy weirdos on myspace, well, it would probably blow your little skull wide open if you knew how much I not only talk about you but how much I think about you.


Okay, some of you.

Just take a quick glance up there and imagine all those columns, or stacks, as PeopleBrowsr likes to call them, moving constantly.  That’s just twitter.   Check out the Google Profile links to the other places I find myself.

Don’t get me wrong, I dig this netizen life.

This connectivity and interestingly awesomesauce people all over the world spitting out ideas and sentiments and projects and roadtrips and Love.  Truly great stuff.

Providing what I think is now the best online community for twenty somethings to the world.  It feels pretty good.

And don’t even get me started on the relationships I’ve plucked off the web.  There’s almost too many to name.

There is too many to name.

But I launched a charity campaign with an incredible woman I’ve never met, and I run a massive community of wonderful people with another young lady I’ve never met.

When I asked for some help, this entire group of people from all over the world raised their hands!

And I know I’m not unique.

When you hang out in any group you realize that amazing people are everywhere.  Everyone’s busy.  Everyone’s got ideas and the best of people shines through the ideas they’re pursuing.  It becomes addictive, seeking out people who think in cool ways.

I’m definitely addicted.

But I also throw myself at projects I believe in like Perez Hilton throws himself at attention.

And when I circle back to the beginning of a run that began with a simple blogger meetup, and now has me trying to make 20 Something Bloggers warm and fuzzy for good honest personal bloggers, all while hoping to integrate my professional life and ever widening network of people worldwide into a manageable, real world of connection and interactivity and friends and resources…

…I find myself finally at a point at which I can take stock of how far I’ve come and what the next few steps might be and


…I’m going to start with a deep breath.